Oxalyl chloride → HCID 18466196, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 ml three-necked flask, oxalyl chloride (1.95 ml, 2.19.10−2 mol, 1 eq.) is added dropwise, under argon, to a solution of the acid obtained in Step D (5 g, 2.17.10−2 mol) in anhydrous dichloromethane (225 ml) at 0° C. A few drops of anhydrous dimethylformamide are then added. After 1 hour at 0° C., slight evolution of gas is still observed and the three-necked flask is left at ambient temperature for 40 minutes. After return to 0° C., aluminium chloride (7.5 g, 5.62.10−2 mol, 2.6 eq.) is added using a spatula. The initially yellow solution becomes red, orange and then khaki-green. After 15 minutes' stirring at 0° C., the mixture is poured into an ice/1N HCl mixture. After separation of the phases and washings of the acidic aqueous phase with dichloromethane, the combined organic phases are washed with water, then treated with a saturated NaHCO3 solution and finally washed with a saturated NaCl solution. After drying over MgSO4 and evaporation under reduced pressure, the yellow oil obtained crystallises in a freezer.

Provenance & Evidence